Ether, ethyl ethynyl → 1-Ethoxyethene-2-boronic acid pinacol ester

HRID 1480801Notes

Reaction equation

HRID 1480801 reaction equation
[CH2:1]([O:3][C:4]#[CH:5])[CH3:2].[BH3:6].[OH:7][C:8]([C:11]([OH:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]>C(Cl)Cl>[CH2:4]([O:3]/[CH:1]=[CH:2]/[B:6]1[O:14][C:11]([CH3:13])([CH3:12])[C:8]([CH3:10])([CH3:9])[O:7]1)[CH3:5]

Participants

4

Reactant 2

HCID 61239Ether, ethyl ethynylHCID 178419189HCID 178419189, compound

Product 1

HCID 219739081-Ethoxyethene-2-boronic acid pinacol esterYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethoxyethyne (60% w/w in hexanes, 30 mL, 154 mmol) in DCM (230 mL) was cooled at 0° C. and pinacol borane (27 mL, 186 mmol) was added followed by Cp2Zr(H)Cl (1.96 g, 7.60 mmol). The mixture was allowed to reach room temperature and stirred for 18 hours. The reaction was filtered through a pad of neutral alumina eluting with 10% EtOAc in cyclohexane to afford the title compound (27.66 g, 91%).

Workup

  1. customto reach room temperature
  2. filtrationThe reaction was filtered through a pad of neutral alumina eluting with 10% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-1080e12234e14f388d6e8a2083c4d37e
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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